Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction

Org Lett. 2013 Feb 1;15(3):444-7. doi: 10.1021/ol303040r. Epub 2013 Jan 15.

Abstract

A stereo- and regioselective Diels-Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds in high yields and diastereoselectivities.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cyclization
  • Cycloaddition Reaction
  • Dihydropyridines / chemistry*
  • Lewis Acids / chemistry
  • Molecular Structure
  • Quinuclidines / chemical synthesis*
  • Quinuclidines / chemistry
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Dihydropyridines
  • Lewis Acids
  • Quinuclidines
  • Rhodium